JP2003081924A - Novel aromatic compound having amino group and organic electroluminescence device using the same - Google Patents

Abstract

(57) [Summary] [PROBLEMS] To provide a light emission luminance and a high color purity even at a low applied voltage.
EL device that emits red light with high light emission efficiency and
Novel aromatization with amino group for use in organic EL devices
Provide compound. SOLUTION: The present invention relates to an agent represented by the following general formula (1).
Novel aromatic compound having a mino group and its use
Device EL element. Embedded image (X in the general formula (1)₁Is a bivalent having 16 to 60 carbon atoms
Condensed aromatic ring, Ar₁~ Ar_FourIs a fragrance having 6 to 30 carbon atoms.
An aromatic ring, Ar₁~ Ar_FourAt least one of
An amino group represented by the following general formula (2). Embedded image (X in the general formula (2)_TwoIs a divalent aromatic having 6 to 30 carbon atoms
Represents an aromatic ring;₁And R _TwoIs an alk having 1 to 30 carbon atoms
And represents an aromatic ring having 6 to 30 carbon atoms. R ₁as well as
R_TwoMay form a ring. ))

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention relates to a novel aromatic compound having an amino group and an organic electroluminescent device, and more particularly to an organic electroluminescent device which emits red light with high color purity, emission brightness and emission efficiency. The present invention relates to a novel aromatic compound used for an organic electroluminescence device.

[0002]

2. Description of the Related Art Organic electroluminescence devices (organic EL devices) using organic substances are promising for use as solid-state light emitting inexpensive large-area full-color display devices, and many developments have been made. An organic EL element is generally composed of a light emitting layer and a pair of counter electrodes sandwiching the layer, and when an electric field is applied between the electrodes, electrons are injected from the cathode side and holes are injected from the anode side. The electrons recombine with holes in the light emitting layer to generate an excited state, and when the excited state returns to the ground state, energy is emitted as light to emit light. Although the organic EL element display is currently in practical use, a full-color display element is under development, and in particular, it has high color purity and luminous efficiency.
There is a demand for a light emitting material for an organic EL device that has a long life and emits red light. As a solution to these problems, for example, Japanese Unexamined Patent Publication (Kokai) No. 8-311442 discloses a red light emitting device in which a naphthacene or pentacene derivative is added to a light emitting layer. However, this light emitting element
Although the red purity was excellent, the applied voltage was as high as 11 V and the half-life time of brightness was about 150 hours, which was insufficient.
Japanese Unexamined Patent Publication (Kokai) No. 3-162481 discloses an element in which a dicyanomethylene (DCM) -based compound is added to a light emitting layer, but the purity of red color is insufficient. JP 2001
Japanese Patent Publication No. 81451 discloses a red light emitting device in which an amine-based aromatic compound is added to a light emitting layer. However, this light emitting device has good CIE chromaticity (0.64, 0.33) and color purity. , The drive voltage was high. Also, WO01 / 2
3497 discloses a device in which an amine-based aromatic compound is added to the light emitting layer, but the emission color was reddish orange and the chromaticity was insufficient.

[0003]

DISCLOSURE OF THE INVENTION The present invention has been made to solve the above-mentioned problems, and has a high color purity, a high emission luminance and a high emission efficiency even at a low applied voltage, and an organic EL emitting a reddish light. It is an object of the present invention to provide a novel aromatic compound having an amino group, which is used for a device and an organic EL device.

[0004]

Means for Solving the Problems As a result of intensive studies to achieve the above-mentioned object, the present inventors have found that an electron-donating group is attached onto an aromatic amino group bonded to a mother skeleton having a specific structure. By further introducing a substituent, it was found that an element having high color purity and capable of emitting light with high luminance and high efficiency at low voltage driving can be provided, and the present invention has been completed.

That is, the present invention provides a novel aromatic compound having an amino group represented by the following general formula (1).

[Chemical 3] (In the general formula (1), X ₁ is a substituted or unsubstituted divalent condensed aromatic ring having 16 to 60 carbon atoms, Ar _{1 to} Ar.
₄ are each independently substituted or unsubstituted 6 carbon atoms
To 30 aromatic rings, and at least one of Ar _{1 to} Ar ₄ is an amino group represented by the following general formula (2).

[0006]

[Chemical 4] (In the general formula (2), X ₂ represents a substituted or unsubstituted divalent aromatic ring having 6 to 30 carbon atoms, R ₁ and R ₂ are each independently a substituted or unsubstituted straight chain, A branched or cyclic alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted aromatic ring having 6 to 30 carbon atoms, R ₁ and R ₂ may form a ring.

Further, the present invention is an organic EL device having a light emitting layer or a plurality of organic compound layers including a light emitting layer between a pair of electrodes, wherein at least one of the organic compound layers is described in claim 1. The present invention provides an organic EL device containing the aromatic compound represented by the general formula (1).

[0008]

BEST MODE FOR CARRYING OUT THE INVENTION The novel aromatic compound of the present invention has the general formula (1) in which X ₁ is a substituted or unsubstituted divalent fused aromatic ring having 16 to 60 carbon atoms, Ar ₁ to Ar
₄ are each independently substituted or unsubstituted 6 carbon atoms
To 30 aromatic rings, and at least one of Ar _{1 to} Ar ₄ is an amino group represented by the general formula (2). Further, in the general formula (2), X ₂ represents a substituted or unsubstituted divalent aromatic ring having 6 to 30 carbon atoms, and R ₁ and R
_2's each independently represent a substituted or unsubstituted linear, branched or cyclic alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted aromatic ring having 6 to 30 carbon atoms.
R ₁ and R ₂ may form a ring.

[0009] In the general formula (1), the carbon number of the substituted or unsubstituted X ₁ is the divalent condensed aromatic rings of 16 to 60, for example, fluoranthene, benzofluoranthene, dibenzo fluoranthene, naphtho Fluoranthene,
Benzodifluoranthene, fluoranthenofluoranthene, acephenanthrylene, aceanthrylene, triphenylene, acenaphthotriphenylene, chrysene, perylene, benzochrysene, dibenzochrysene, naphthacene, preaden, picene, pentaphene, pentacene, tetraphenylene, Hexaphene, hexacene, coronene, trinaphthylene, heptaphene, heptaphene, pyranthrene, ovalen, benzophenanthrene, dibenzonaphthacene, benzanthracene, dibenzanthracene, benzonaphthacene, naphthopyrene, benzopyrene, benzopicene, dibenzopicene, dibenzopyrene, benzopentacene, Benzocyclooctene, dibenzopentacene, anthranaphthacene, fluoranthenoaceanthrylene, ace Shift fluoranthene, indenoperylene, diindenoperylene, Benzoteriren,
Examples include dibenzoterylene, naphthoaceanthrylene, fluoranthenotriphenylene and the like. Preferably, fluoranthene, acenaphthofluoranthene, naphthacene,
It is perylene.

Examples of the substituent of the condensed aromatic ring include a halogen atom, a hydroxyl group, a substituted or unsubstituted amino group, a nitro group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted group. Alkenyl group, substituted or unsubstituted cycloalkyl group, substituted or unsubstituted alkoxy group, substituted or unsubstituted aromatic hydrocarbon group, substituted or unsubstituted aromatic heterocyclic group, substituted or unsubstituted aralkyl group , A substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkoxycarbonyl group, and a carboxyl group, and the substitution position of the condensed ring and the number of substitutions are not particularly limited. Examples of the halogen atom include fluorine, chlorine, bromine and iodine.

The substituted or unsubstituted amino group is -NX ₃
X ₄ is represented, and X ₃ and X ₄ are each independently, for example, hydrogen atom, methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, s-butyl group, isobutyl group, t- Butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, hydroxymethyl group, 1-hydroxyethyl group, 2-hydroxyethyl group, 2-hydroxyisobutyl group, 1,2-dihydroxy group Ethyl group, 1,3-dihydroxyisopropyl group, 2,3-dihydroxy-t-butyl group, 1,2,3
-Trihydroxypropyl group, chloromethyl group, 1-chloroethyl group, 2-chloroethyl group, 2-chloroisobutyl group, 1,2-dichloroethyl group, 1,3-dichloroisopropyl group, 2,3-dichloro-t- Butyl group,
1,2,3-trichloropropyl group, bromomethyl group,
1-bromoethyl group, 2-bromoethyl group, 2-bromoisobutyl group, 1,2-dibromoethyl group, 1,3-dibromoisopropyl group, 2,3-dibromo-t-butyl group, 1,2,3-tri Bromopropyl group, iodomethyl group, 1-iodoethyl group, 2-iodoethyl group, 2-iodoisobutyl group, 1,2-diiodoethyl group, 1,3
-Diiodoisopropyl group, 2,3-diiodo-t-butyl group, 1,2,3-triiodopropyl group, aminomethyl group, 1-aminoethyl group, 2-aminoethyl group, 2
-Aminoisobutyl group, 1,2-diaminoethyl group,
1,3-diaminoisopropyl group, 2,3-diamino-
t-butyl group, 1,2,3-triaminopropyl group, cyanomethyl group, 1-cyanoethyl group, 2-cyanoethyl group, 2-cyanoisobutyl group, 1,2-dicyanoethyl group, 1,3-dicyanoisopropyl group , 2,3-dicyano-t-butyl group, 1,2,3-tricyanopropyl group, nitromethyl group, 1-nitroethyl group, 2-nitroethyl group, 2-nitroisobutyl group, 1,2-dinitroethyl group, 1,3-dinitroisopropyl group, 2,3-
Dinitro-t-butyl group, 1,2,3-trinitropropyl group, phenyl group, 1-naphthyl group, 2-naphthyl group, 1-anthryl group, 2-anthryl group, 9-anthryl group, 1-phenanthryl group , 2-phenanthryl group, 3-phenanthryl group, 4-phenanthryl group, 9
-Phenanthryl group, 1-naphthacenyl group, 2-naphthacenyl group, 9-naphthacenyl group, 4-styrylphenyl group, 1-pyrenyl group, 2-pyrenyl group, 4-pyrenyl group, 2-biphenylyl group, 3-biphenylyl group Base, 4
-Biphenylyl group, p-terphenyl-4-yl group,
p-terphenyl-3-yl group, p-terphenyl-2
-Yl group, m-terphenyl-4-yl group, m-terphenyl-3-yl group, m-terphenyl-2-yl group,
o-tolyl group, m-tolyl group, p-tolyl group, pt-
Butylphenyl group, p- (2-phenylpropyl) phenyl group, 3-methyl-2-naphthyl group, 4-methyl-1
-Naphthyl group, 4-methyl-1-anthryl group, 4'-
Methylbiphenylyl group, 4 ″ -t-butyl-p-terphenyl-4-yl group, 2-pyrrolyl group, 3-pyrrolyl group, pyrazinyl group, 2-pyridinyl group, 3-pyridinyl group, 4-pyridinyl group , 2-indolyl group, 3-indolyl group, 4-indolyl group, 5-indolyl group, 6-indolyl group, 7-indolyl group, 1-isoindolyl group, 3-isoindolyl group, 4-isoindolyl group, 5
-Isoindolyl group, 6-isoindolyl group, 7-isoindolyl group, 2-furyl group, 3-furyl group, 2-benzofuranyl group, 3-benzofuranyl group, 4-benzofuranyl group, 5-benzofuranyl group, 6-benzofuranyl group, 7 -Benzofuranyl group, 1-isobenzofuranyl group, 3-isobenzofuranyl group, 4-isobenzofuranyl group, 5-isobenzofuranyl group, 6-isobenzofuranyl group, 7-isobenzofuranyl group Group, 2-quinolyl group,
3-quinolyl group, 4-quinolyl group, 5-quinolyl group, 6
-Quinolyl group, 7-quinolyl group, 8-quinolyl group, 1-
Isoquinolyl group, 3-isoquinolyl group, 4-isoquinolyl group, 5-isoquinolyl group, 6-isoquinolyl group, 7-
Isoquinolyl group, 8-isoquinolyl group, 2-quinoxalinyl group, 5-quinoxalinyl group, 6-quinoxalinyl group, 1-carbazolyl group, 2-carbazolyl group, 3-carbazolyl group, 4-carbazolyl group, 1-phenanthridinyl group , 2-phenanthridinyl group, 3-phenanthridinyl group, 4-phenanthridinyl group, 6-phenanthridinyl group, 7-phenanthridinyl group, 8-phenanthridinyl group, 9 -Phenanthridinyl group, 10-phenanthridinyl group, 1-acridinyl group, 2-acridinyl group, 3-acridinyl group, 4-acridinyl group,
9-acridinyl group, 1,7-phenanthroline-2-
Yl group, 1,7-phenanthrolin-3-yl group, 1,
7-phenanthrolin-4-yl group, 1,7-phenanthrolin-5-yl group, 1,7-phenanthroline-6
-Yl group, 1,7-phenanthroline-8-yl group,
1,7-phenanthrolin-9-yl group, 1,7-phenanthrolin-10-yl group, 1,8-phenanthrolin-2-yl group, 1,8-phenanthrolin-3-yl group Group, 1,8-phenanthrolin-4-yl group, 1,8-
Phenanthrolin-5-yl group, 1,8-phenanthrolin-6-yl group, 1,8-phenanthrolin-7-yl group, 1,8-phenanthrolin-9-yl group, 1, 8
-Phenanthroline-10-yl group, 1,9-phenanthroline-2-yl group, 1,9-phenanthroline-3
-Yl group, 1,9-phenanthrolin-4-yl group,
1,9-phenanthrolin-5-yl group, 1,9-phenanthrolin-6-yl group, 1,9-phenanthrolin-7-yl group, 1,9-phenanthrolin-8-yl Group, 1,9-phenanthrolin-10-yl group, 1,1
0-phenanthrolin-2-yl group, 1,10-phenanthrolin-3-yl group, 1,10-phenanthrolin-4-yl group, 1,10-phenanthrolin-5-yl group, 2,9-phenanthrolin-1-yl group, 2,9-
Phenanthrolin-3-yl group, 2,9-phenanthrolin-4-yl group, 2,9-phenanthrolin-5-yl group, 2,9-phenanthrolin-6-yl group, 2, 9
-Phenanthroline-7-yl group, 2,9-phenanthroline-8-yl group, 2,9-phenanthroline-10
-Yl group, 2,8-phenanthrolin-1-yl group,
2,8-phenanthrolin-3-yl group, 2,8-phenanthrolin-4-yl group, 2,8-phenanthrolin-5-yl group, 2,8-phenanthrolin-6-yl group Group, 2,8-phenanthrolin-7-yl group, 2,8-
Phenanthrolin-9-yl group, 2,8-phenanthrolin-10-yl group, 2,7-phenanthroline-1-
Yl group, 2,7-phenanthrolin-3-yl group, 2,
7-phenanthrolin-4-yl group, 2,7-phenanthrolin-5-yl group, 2,7-phenanthroline-6
-Yl group, 2,7-phenanthrolin-8-yl group,
2,7-phenanthrolin-9-yl group, 2,7-phenanthrolin-10-yl group, 1-phenazinyl group, 2
-Phenazinyl group, 1-phenothiazinyl group, 2-phenothiazinyl group, 3-phenothiazinyl group, 4-phenothiazinyl group, 1-phenoxazinyl group, 2-phenoxazinyl group, 3-phenoxazinyl group, 4-phenoxazinyl group, 2- Oxazolyl group, 4-oxazolyl group,
5-oxazolyl group, 2-oxadiazolyl group, 5-oxadiazolyl group, 3-flazanyl group, 2-thienyl group, 3-thienyl group, 2-methylpyrrol-1-yl group, 2-methylpyrrol-3-yl group, 2-methylpyrrol-4-yl group, 2-methylpyrrol-5-yl group,
3-methylpyrrol-1-yl group, 3-methylpyrrol-2-yl group, 3-methylpyrrol-4-yl group, 3-
Methylpyrrol-5-yl group, 2-t-butylpyrrol-4-yl group, 3- (2-phenylpropyl) pyrrol-1-yl group, 2-methyl-1-indolyl group, 4-methyl-1- Indolyl group, 2-methyl-3-indolyl group, 4-methyl-3-indolyl group, 2-t-butyl 1
-Indolyl group, 4-t-butyl 1-indolyl group, 2
-T-butyl-3-indolyl group, 4-t-butyl-3
-Indolyl groups and the like.

As the substituted or unsubstituted alkyl group, for example, methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, s-butyl group, isobutyl group, t-butyl group, n-pentyl group, an n-hexyl group,
n-heptyl group, n-octyl group, hydroxymethyl group, 1-hydroxyethyl group, 2-hydroxyethyl group, 2-hydroxyisobutyl group, 1,2-dihydroxyethyl group, 1,3-dihydroxyisopropyl group,
2,3-dihydroxy-t-butyl group, 1,2,3-trihydroxypropyl group, chloromethyl group, 1-chloroethyl group, 2-chloroethyl group, 2-chloroisobutyl group, 1,2-dichloroethyl group, 1,3-dichloroisopropyl group, 2,3-dichloro-t-butyl group, 1,
2,3-trichloropropyl group, bromomethyl group, 1-
Bromoethyl group, 2-bromoethyl group, 2-bromoisobutyl group, 1,2-dibromoethyl group, 1,3-dibromoisopropyl group, 2,3-dibromo-t-butyl group,
1,2,3-tribromopropyl group, iodomethyl group,
1-iodoethyl group, 2-iodoethyl group, 2-iodoisobutyl group, 1,2-diiodoethyl group, 1,3-diiodoisopropyl group, 2,3-diiodo-t-butyl group, 1,2,3-tri Iodopropyl group, aminomethyl group, 1-aminoethyl group, 2-aminoethyl group, 2-aminoisobutyl group, 1,2-diaminoethyl group, 1,3
-Diaminoisopropyl group, 2,3-diamino-t-butyl group, 1,2,3-triaminopropyl group, cyanomethyl group, 1-cyanoethyl group, 2-cyanoethyl group, 2
-Cyanoisobutyl group, 1,2-dicyanoethyl group,
1,3-dicyanoisopropyl group, 2,3-dicyano-
t-butyl group, 1,2,3-tricyanopropyl group, nitromethyl group, 1-nitroethyl group, 2-nitroethyl group, 2-nitroisobutyl group, 1,2-dinitroethyl group, 1,3-dinitroisopropyl group , 2,3-dinitro-t-butyl group, 1,2,3-trinitropropyl group and the like.

Examples of the substituted or unsubstituted alkenyl group include vinyl group, allyl group, 1-butenyl group, 2
-Butenyl group, 3-butenyl group, 1,3-butanedienyl group, 1-methylvinyl group, styryl group, 2,2-diphenylvinyl group, 1,2-diphenylvinyl group, 1-methylallyl group, 1,1- Dimethylallyl group, 2-methylallyl group, 1-phenylallyl group, 2-phenylallyl group, 3-phenylallyl group, 3,3-diphenylallyl group, 1,2-dimethylallyl group, 1-phenyl-1-butenyl Group, 3-phenyl-1-butenyl group and the like.

Examples of the substituted or unsubstituted cycloalkyl group include cyclopropyl group, cyclobutyl group,
Examples thereof include cyclopentyl group, cyclohexyl group, 4-methylcyclohexyl group and the like.

The substituted or unsubstituted alkoxy group is --O.
Represented by Y _1, as the Y _1, for example, a methyl group, an ethyl group, a propyl group, an isopropyl group, n- butyl group, s
-Butyl group, isobutyl group, t-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, hydroxymethyl group, 1-hydroxyethyl group, 2
-Hydroxyethyl group, 2-hydroxyisobutyl group,
1,2-dihydroxyethyl group, 1,3-dihydroxyisopropyl group, 2,3-dihydroxy-t-butyl group, 1,2,3-trihydroxypropyl group, chloromethyl group, 1-chloroethyl group, 2-chloroethyl group Base, 2
-Chloroisobutyl group, 1,2-dichloroethyl group,
1,3-dichloroisopropyl group, 2,3-dichloro-
t-butyl group, 1,2,3-trichloropropyl group, bromomethyl group, 1-bromoethyl group, 2-bromoethyl group, 2-bromoisobutyl group, 1,2-dibromoethyl group, 1,3-dibromoisopropyl group, 2,3-dibromo-t-butyl group, 1,2,3-tribromopropyl group, iodomethyl group, 1-iodoethyl group, 2-iodoethyl group, 2-iodoisobutyl group, 1,2-diiodoethyl group, 1, 3-diiodoisopropyl group, 2,3-
Diiodo-t-butyl group, 1,2,3-triiodopropyl group, aminomethyl group, 1-aminoethyl group, 2-aminoethyl group, 2-aminoisobutyl group, 1,2-diaminoethyl group, 1, 3-diaminoisopropyl group, 2,
3-diamino-t-butyl group, 1,2,3-triaminopropyl group, cyanomethyl group, 1-cyanoethyl group, 2
-Cyanoethyl group, 2-cyanoisobutyl group, 1,2-
Dicyanoethyl group, 1,3-dicyanoisopropyl group,
2,3-dicyano-t-butyl group, 1,2,3-tricyanopropyl group, nitromethyl group, 1-nitroethyl group, 2-nitroethyl group, 2-nitroisobutyl group,
1,2-dinitroethyl group, 1,3-dinitroisopropyl group, 2,3-dinitro-t-butyl group, 1,2,3
-Trinitropropyl group and the like.

Examples of the substituted or unsubstituted aromatic hydrocarbon group include phenyl group, 1-naphthyl group, 2-naphthyl group, 1-anthryl group, 2-anthryl group, 9-
Anthryl group, 1-phenanthryl group, 2-phenanthryl group, 3-phenanthryl group, 4-phenanthryl group, 9-phenanthryl group, 1-naphthacenyl group, 2-
Naphthalcenyl group, 9-naphthacenyl group, 1-pyrenyl group, 2-pyrenyl group, 4-pyrenyl group, 2-biphenylyl group, 3-biphenylyl group, 4-biphenylyl group, p-terphenyl-4-yl group , P-terphenyl-3-yl group, p-terphenyl-2-yl group, m-terphenyl-4-yl group, m-terphenyl-3-yl group, m-terphenyl-2-yl group , O-tolyl group, m
-Tolyl group, p-tolyl group, pt-butylphenyl group, p- (2-phenylpropyl) phenyl group, 3-methyl-2-naphthyl group, 4-methyl-1-naphthyl group,
4-methyl-1-anthryl group, 4′-methylbiphenylyl group, 4 ″ -t-butyl-p-terphenyl-4-
Examples thereof include an yl group.

Examples of the substituted or unsubstituted aromatic heterocyclic group include, for example, 1-pyrrolyl group, 2-pyrrolyl group and 3-pyrrolyl group.
Pyrrolyl group, pyrazinyl group, 2-pyridinyl group, 3-pyridinyl group, 4-pyridinyl group, 1-indolyl group, 2
-Indolyl group, 3-indolyl group, 4-indolyl group, 5-indolyl group, 6-indolyl group, 7-indolyl group, 1-isoindolyl group, 2-isoindolyl group, 3-isoindolyl group, 4-isoindolyl group, 5
-Isoindolyl group, 6-isoindolyl group, 7-isoindolyl group, 2-furyl group, 3-furyl group, 2-benzofuranyl group, 3-benzofuranyl group, 4-benzofuranyl group, 5-benzofuranyl group, 6-benzofuranyl group, 7 -Benzofuranyl group, 1-isobenzofuranyl group, 3-isobenzofuranyl group, 4-isobenzofuranyl group, 5-isobenzofuranyl group, 6-isobenzofuranyl group, 7-isobenzofuranyl group Group, 2-quinolyl group,
3-quinolyl group, 4-quinolyl group, 5-quinolyl group, 6
-Quinolyl group, 7-quinolyl group, 8-quinolyl group, 1-
Isoquinolyl group, 3-isoquinolyl group, 4-isoquinolyl group, 5-isoquinolyl group, 6-isoquinolyl group, 7-
Isoquinolyl group, 8-isoquinolyl group, 2-quinoxalinyl group, 5-quinoxalinyl group, 6-quinoxalinyl group, 1-carbazolyl group, 2-carbazolyl group, 3-carbazolyl group, 4-carbazolyl group, 9-carbazolyl group, 1- Phenanthridinyl group, 2-phenanthridinyl group, 3-phenanthridinyl group, 4-phenanthridinyl group, 6-phenanthridinyl group, 7-phenanthridinyl group, 8-phenance Ridinyl group, 9-phenanthridinyl group, 10-phenanthridinyl group, 1-acridinyl group, 2-acridinyl group, 3-acridinyl group,
4-acridinyl group, 9-acridinyl group, 1,7-phenanthrolin-2-yl group, 1,7-phenanthrolin-3-yl group, 1,7-phenanthrolin-4-yl group, 1 , 7-phenanthrolin-5-yl group, 1,7-
Phenanthrolin-6-yl group, 1,7-phenanthrolin-8-yl group, 1,7-phenanthrolin-9-yl group, 1,7-phenanthrolin-10-yl group, 1,
8-phenanthrolin-2-yl group, 1,8-phenanthrolin-3-yl group, 1,8-phenanthroline-4
-Yl group, 1,8-phenanthrolin-5-yl group,
1,8-phenanthrolin-6-yl group, 1,8-phenanthrolin-7-yl group, 1,8-phenanthrolin-9-yl group, 1,8-phenanthrolin-10-yl Group, 1,9-phenanthrolin-2-yl group, 1,9-
Phenanthrolin-3-yl group, 1,9-phenanthrolin-4-yl group, 1,9-phenanthrolin-5-yl group, 1,9-phenanthrolin-6-yl group, 1, 9
-Phenanthroline-7-yl group, 1,9-phenanthroline-8-yl group, 1,9-phenanthroline-10
-Yl group, 1,10-phenanthrolin-2-yl group,
1,10-phenanthrolin-3-yl group, 1,10-
Phenanthrolin-4-yl group, 1,10-phenanthrolin-5-yl group, 2,9-phenanthroline-1-
Yl group, 2,9-phenanthrolin-3-yl group, 2,
9-phenanthrolin-4-yl group, 2,9-phenanthrolin-5-yl group, 2,9-phenanthroline-6
-Yl group, 2,9-phenanthroline-7-yl group,
2,9-phenanthrolin-8-yl group, 2,9-phenanthrolin-10-yl group, 2,8-phenanthrolin-1-yl group, 2,8-phenanthrolin-3-yl group Group, 2,8-phenanthrolin-4-yl group, 2,8-
Phenanthrolin-5-yl group, 2,8-phenanthrolin-6-yl group, 2,8-phenanthrolin-7-yl group, 2,8-phenanthrolin-9-yl group, 2, 8
-Phenanthrolin-10-yl group, 2,7-phenanthrolin-1-yl group, 2,7-phenanthroline-3
-Yl group, 2,7-phenanthrolin-4-yl group,
2,7-phenanthrolin-5-yl group, 2,7-phenanthrolin-6-yl group, 2,7-phenanthrolin-8-yl group, 2,7-phenanthrolin-9-yl Group, 2,7-phenanthrolin-10-yl group, 1-phenazinyl group, 2-phenazinyl group, 1-phenothiazinyl group, 2-phenothiazinyl group, 3-phenothiazinyl group, 4-phenothiazinyl group, 10 -Phenothiazinyl group, 1-phenoxazinyl group, 2-phenoxazinyl group, 3-phenoxazinyl group, 4-phenoxazinyl group, 10-phenoxazinyl group, 2-oxazolyl group,
4-oxazolyl group, 5-oxazolyl group, 2-oxadiazolyl group, 5-oxadiazolyl group, 3-flazanyl group, 2-thienyl group, 3-thienyl group, 2-methylpyrrol-1-yl group, 2-methylpyrrole- 3-yl group, 2-methylpyrrol-4-yl group, 2-methylpyrrol-5-yl group, 3-methylpyrrol-1-yl group,
3-methylpyrrol-2-yl group, 3-methylpyrrol-4-yl group, 3-methylpyrrol-5-yl group, 2-
t-butylpyrrol-4-yl group, 3- (2-phenylpropyl) pyrrol-1-yl group, 2-methyl-1-indolyl group, 4-methyl-1-indolyl group, 2-methyl-3-indolyl group Group, 4-methyl-3-indolyl group, 2-t-butyl 1-indolyl group, 4-t-butyl 1-indolyl group, 2-t-butyl-3-indolyl group, 4-t-butyl-3- Examples include indolyl groups.

Examples of the substituted or unsubstituted aralkyl group include benzyl group, 1-phenylethyl group and 2-
Phenylethyl group, 1-phenylisopropyl group, 2-
Phenyl isopropyl group, phenyl-t-butyl group, α
-Naphthylmethyl group, 1-α-naphthylethyl group, 2-
α-naphthylethyl group, 1-α-naphthylisopropyl group, 2-α-naphthylisopropyl group, β-naphthylmethyl group, 1-β-naphthylethyl group, 2-β-naphthylethyl group, 1-β-naphthylisopropyl group Group, 2-β-
Naphthylisopropyl group, 1-pyrrolylmethyl group, 2-
(1-Pyrrolyl) ethyl group, p-methylbenzyl group, m
-Methylbenzyl group, o-methylbenzyl group, p-chlorobenzyl group, m-chlorobenzyl group, o-chlorobenzyl group, p-bromobenzyl group, m-bromobenzyl group, o-bromobenzyl group, p-iodo Benzyl group, m
-Iodobenzyl group, o-iodobenzyl group, p-hydroxybenzyl group, m-hydroxybenzyl group, o-hydroxybenzyl group, p-aminobenzyl group, m-aminobenzyl group, o-aminobenzyl group, p-nitro Benzyl group, m-nitrobenzyl group, o-nitrobenzyl group, p-cyanobenzyl group, m-cyanobenzyl group, o
-Cyanobenzyl group, 1-hydroxy-2-phenylisopropyl group, 1-chloro-2-phenylisopropyl group and the like can be mentioned.

The substituted or unsubstituted aryloxy group is represented by -OZ, and Z is, for example, a phenyl group, 1
-Naphthyl group, 2-naphthyl group, 1-anthryl group, 2
-Anthryl group, 9-anthryl group, 1-phenanthryl group, 2-phenanthryl group, 3-phenanthryl group,
4-phenanthryl group, 9-phenanthryl group, 1-naphthacenyl group, 2-naphthacenyl group, 9-naphthacenyl group, 1-pyrenyl group, 2-pyrenyl group, 4-pyrenyl group, 2-biphenylyl group, 3-biphenylyl group Base, 4
-Biphenylyl group, p-terphenyl-4-yl group,
p-terphenyl-3-yl group, p-terphenyl-2
-Yl group, m-terphenyl-4-yl group, m-terphenyl-3-yl group, m-terphenyl-2-yl group,
o-tolyl group, m-tolyl group, p-tolyl group, pt-
Butylphenyl group, p- (2-phenylpropyl) phenyl group, 3-methyl-2-naphthyl group, 4-methyl-1
-Naphthyl group, 4-methyl-1-anthryl group, 4'-
Methylbiphenylyl group, 4 ″ -t-butyl-p-terphenyl-4-yl group, 2-pyrrolyl group, 3-pyrrolyl group, pyrazinyl group, 2-pyridinyl group, 3-pyridinyl group, 4-pyridinyl group , 2-indolyl group, 3-indolyl group, 4-indolyl group, 5-indolyl group, 6-indolyl group, 7-indolyl group, 1-isoindolyl group, 3-isoindolyl group, 4-isoindolyl group, 5
-Isoindolyl group, 6-isoindolyl group, 7-isoindolyl group, 2-furyl group, 3-furyl group, 2-benzofuranyl group, 3-benzofuranyl group, 4-benzofuranyl group, 5-benzofuranyl group, 6-benzofuranyl group, 7 -Benzofuranyl group, 1-isobenzofuranyl group, 3-isobenzofuranyl group, 4-isobenzofuranyl group, 5-isobenzofuranyl group, 6-isobenzofuranyl group, 7-isobenzofuranyl group Group, 2-quinolyl group,
3-quinolyl group, 4-quinolyl group, 5-quinolyl group, 6
-Quinolyl group, 7-quinolyl group, 8-quinolyl group, 1-
Isoquinolyl group, 3-isoquinolyl group, 4-isoquinolyl group, 5-isoquinolyl group, 6-isoquinolyl group, 7-
Isoquinolyl group, 8-isoquinolyl group, 2-quinoxalinyl group, 5-quinoxalinyl group, 6-quinoxalinyl group, 1-carbazolyl group, 2-carbazolyl group, 3-carbazolyl group, 4-carbazolyl group, 1-phenanthridinyl group , 2-phenanthridinyl group, 3-phenanthridinyl group, 4-phenanthridinyl group, 6-phenanthridinyl group, 7-phenanthridinyl group, 8-phenanthridinyl group, 9 -Phenanthridinyl group, 10-phenanthridinyl group, 1-acridinyl group, 2-acridinyl group, 3-acridinyl group, 4-acridinyl group,
9-acridinyl group, 1,7-phenanthroline-2-
Yl group, 1,7-phenanthrolin-3-yl group, 1,
7-phenanthrolin-4-yl group, 1,7-phenanthrolin-5-yl group, 1,7-phenanthroline-6
-Yl group, 1,7-phenanthroline-8-yl group,
1,7-phenanthrolin-9-yl group, 1,7-phenanthrolin-10-yl group, 1,8-phenanthrolin-2-yl group, 1,8-phenanthrolin-3-yl group Group, 1,8-phenanthrolin-4-yl group, 1,8-
Phenanthrolin-5-yl group, 1,8-phenanthrolin-6-yl group, 1,8-phenanthrolin-7-yl group, 1,8-phenanthrolin-9-yl group, 1, 8
-Phenanthroline-10-yl group, 1,9-phenanthroline-2-yl group, 1,9-phenanthroline-3
-Yl group, 1,9-phenanthrolin-4-yl group,
1,9-phenanthrolin-5-yl group, 1,9-phenanthrolin-6-yl group, 1,9-phenanthrolin-7-yl group, 1,9-phenanthrolin-8-yl Group, 1,9-phenanthrolin-10-yl group, 1,1
0-phenanthrolin-2-yl group, 1,10-phenanthrolin-3-yl group, 1,10-phenanthrolin-4-yl group, 1,10-phenanthrolin-5-yl group, 2,9-phenanthrolin-1-yl group, 2,9-
Phenanthrolin-3-yl group, 2,9-phenanthrolin-4-yl group, 2,9-phenanthrolin-5-yl group, 2,9-phenanthrolin-6-yl group, 2, 9
-Phenanthroline-7-yl group, 2,9-phenanthroline-8-yl group, 2,9-phenanthroline-10
-Yl group, 2,8-phenanthrolin-1-yl group,
2,8-phenanthrolin-3-yl group, 2,8-phenanthrolin-4-yl group, 2,8-phenanthrolin-5-yl group, 2,8-phenanthrolin-6-yl group Group, 2,8-phenanthrolin-7-yl group, 2,8-
Phenanthrolin-9-yl group, 2,8-phenanthrolin-10-yl group, 2,7-phenanthroline-1-
Yl group, 2,7-phenanthrolin-3-yl group, 2,
7-phenanthrolin-4-yl group, 2,7-phenanthrolin-5-yl group, 2,7-phenanthroline-6
-Yl group, 2,7-phenanthrolin-8-yl group,
2,7-phenanthrolin-9-yl group, 2,7-phenanthrolin-10-yl group, 1-phenazinyl group, 2
-Phenazinyl group, 1-phenothiazinyl group, 2-phenothiazinyl group, 3-phenothiazinyl group, 4-phenothiazinyl group, 1-phenoxazinyl group, 2-phenoxazinyl group, 3-phenoxazinyl group, 4-phenoxazinyl group, 2- Oxazolyl group, 4-oxazolyl group,
5-oxazolyl group, 2-oxadiazolyl group, 5-oxadiazolyl group, 3-flazanyl group, 2-thienyl group, 3-thienyl group, 2-methylpyrrol-1-yl group, 2-methylpyrrol-3-yl group, 2-methylpyrrol-4-yl group, 2-methylpyrrol-5-yl group,
3-methylpyrrol-1-yl group, 3-methylpyrrol-2-yl group, 3-methylpyrrol-4-yl group, 3-
Methylpyrrol-5-yl group, 2-t-butylpyrrol-4-yl group, 3- (2-phenylpropyl) pyrrol-1-yl group, 2-methyl-1-indolyl group, 4-methyl-1- Indolyl group, 2-methyl-3-indolyl group, 4-methyl-3-indolyl group, 2-t-butyl 1
-Indolyl group, 4-t-butyl 1-indolyl group, 2
-T-butyl-3-indolyl group, 4-t-butyl-3
-Indolyl groups and the like.

The substituted or unsubstituted alkoxycarbonyl group is represented by --COOY _2, and Y ₂ is, for example,
Methyl group, ethyl group, propyl group, isopropyl group, n
-Butyl group, s-butyl group, isobutyl group, t-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, hydroxymethyl group, 1-hydroxyethyl group, 2-hydroxy group Ethyl group, 2-hydroxyisobutyl group, 1,2-dihydroxyethyl group, 1,
3-dihydroxyisopropyl group, 2,3-dihydroxy-t-butyl group, 1,2,3-trihydroxypropyl group, chloromethyl group, 1-chloroethyl group, 2-chloroethyl group, 2-chloroisobutyl group, 1, 2-dichloroethyl group, 1,3-dichloroisopropyl group, 2,3
-Dichloro-t-butyl group, 1,2,3-trichloropropyl group, bromomethyl group, 1-bromoethyl group, 2-
Bromoethyl group, 2-bromoisobutyl group, 1,2-dibromoethyl group, 1,3-dibromoisopropyl group,
2,3-dibromo-t-butyl group, 1,2,3-tribromopropyl group, iodomethyl group, 1-iodoethyl group, 2-iodoethyl group, 2-iodoisobutyl group,
1,2-diiodoethyl group, 1,3-diiodoisopropyl group, 2,3-diiodo-t-butyl group, 1,2,3
-Triiodopropyl group, aminomethyl group, 1-aminoethyl group, 2-aminoethyl group, 2-aminoisobutyl group, 1,2-diaminoethyl group, 1,3-diaminoisopropyl group, 2,3-diamino- group t-butyl group, 1,
2,3-triaminopropyl group, cyanomethyl group, 1-
Cyanoethyl group, 2-cyanoethyl group, 2-cyanoisobutyl group, 1,2-dicyanoethyl group, 1,3-dicyanoisopropyl group, 2,3-dicyano-t-butyl group,
1,2,3-tricyanopropyl group, nitromethyl group,
1-nitroethyl group, 2-nitroethyl group, 2-nitroisobutyl group, 1,2-dinitroethyl group, 1,3-dinitroisopropyl group, 2,3-dinitro-t-butyl group, 1,2,3-tri Examples thereof include a nitropropyl group.

Ar in the general formula (1)₁~ Ar_FourLine up
And R in the general formula (2)₁And R ₂Replaced or nothing
Each of the substituted aromatic ring having 6 to 30 carbon atoms is independently.
In addition, for example, phenyl group, 1-naphthyl group, 2-naphthyl group
Cyl group, 1-anthryl group, 2-anthryl group, 9-a
Anthryl group, 1-phenanthryl group, 2-phenanthryl group
Group, 3-phenanthryl group, 4-phenanthryl group,
9-phenanthryl group, 1-naphthacenyl group, 2-naphth
Tacenyl group, 9-naphthacenyl group, 1-pyrenyl group, 2
-Pyrenyl group, 4-pyrenyl group, 2-biphenylyl
Group, 3-biphenylyl group, 4-biphenylyl group, p
-Terphenyl-4-yl group, p-terphenyl-3-
Yl group, p-terphenyl-2-yl group, m-terfe
Nyl-4-yl group, m-terphenyl-3-yl group, m
-Terphenyl-2-yl group, o-tolyl group, m-tri
Group, p-tolyl group, pt-butylphenyl group, p-
(2-Phenylpropyl) phenyl group, 3-methyl-2
-Naphthyl group, 4-methyl-1-naphthyl group, 4-methyl group
Ru-1-anthryl group, 4'-methylbiphenylyl
Group, 4 ″ -t-butyl-p-terphenyl-4-yl group
Etc. X in the general formula (2)₂Replace if
Or as an unsubstituted divalent aromatic ring having 6 to 30 carbon atoms
Include divalent aromatic rings.

As the substituted or unsubstituted linear or branched alkyl group having 1 to 30 carbon atoms represented by R ₁ and R ₂ in the general formula (2), methyl group, ethyl group, propyl group, isopropyl group, n- Butyl group, s-butyl group, isobutyl group, t-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, hydroxymethyl group, 1-hydroxyethyl group, 2-hydroxyethyl group Group, 2-hydroxyisobutyl group, 1,2-dihydroxyethyl group, 1,3-dihydroxyisopropyl group,
2,3-dihydroxy-t-butyl group, 1,2,3-trihydroxypropyl group, chloromethyl group, 1-chloroethyl group, 2-chloroethyl group, 2-chloroisobutyl group, 1,2-dichloroethyl group, 1,3-dichloroisopropyl group, 2,3-dichloro-t-butyl group, 1,
2,3-trichloropropyl group, bromomethyl group, 1-
Bromoethyl group, 2-bromoethyl group, 2-bromoisobutyl group, 1,2-dibromoethyl group, 1,3-dibromoisopropyl group, 2,3-dibromo-t-butyl group,
1,2,3-tribromopropyl group, iodomethyl group,
1-iodoethyl group, 2-iodoethyl group, 2-iodoisobutyl group, 1,2-diiodoethyl group, 1,3-diiodoisopropyl group, 2,3-diiodo-t-butyl group, 1,2,3-tri Iodopropyl group, aminomethyl group, 1-aminoethyl group, 2-aminoethyl group, 2-aminoisobutyl group, 1,2-diaminoethyl group, 1,3
-Diaminoisopropyl group, 2,3-diamino-t-butyl group, 1,2,3-triaminopropyl group, cyanomethyl group, 1-cyanoethyl group, 2-cyanoethyl group, 2
-Cyanoisobutyl group, 1,2-dicyanoethyl group,
1,3-dicyanoisopropyl group, 2,3-dicyano-
t-butyl group, 1,2,3-tricyanopropyl group, nitromethyl group, 1-nitroethyl group, 2-nitroethyl group, 2-nitroisobutyl group, 1,2-dinitroethyl group, 1,3-dinitroisopropyl group , 2,3-dinitro-t-butyl group, 1,2,3-trinitropropyl group and the like. In addition, examples of the cyclic alkyl group include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and a 4-methylcyclohexyl group. Examples of the divalent group in which R ₁ and R ₂ form a ring include, for example, tetramethylene group, pentamethylene group, hexamethylene group, diphenylmethane-
2,2'-diyl group, diphenylethane-3,3'-diyl group, diphenylpropane-4,4'-diyl group and the like can be mentioned. The novel aromatic compound having an amino group of the present invention is preferably a light emitting compound.

Specific examples of the aromatic compound represented by the general formula (1) of the present invention are shown below, but the present invention is not limited to these exemplified compounds. In the formula, Me is a methyl group.

[0024]

[Chemical 5]

[0025]

[Chemical 6]

The organic EL device of the present invention is a device in which one or more organic compound layers are formed between an anode and a cathode. In the case of the single layer type, a light emitting layer is provided between the anode and the cathode. The light emitting layer contains a light emitting material, and may further contain a hole injecting material or an electron injecting material for transporting holes injected from the anode or electrons injected from the cathode to the light emitting material. However, it is preferable that the light emitting material has extremely high fluorescence quantum efficiency, high hole transporting ability and electron transporting ability, and forms a uniform thin film. A multilayer organic EL device has a multilayer structure of anode / hole injection layer / light emitting layer / cathode, anode / light emitting layer / electron injection layer / cathode, anode / hole injection layer / light emitting layer / electron injection layer / cathode. Some are stacked.

If necessary, in addition to the compound represented by the general formula of the present invention, further known light emitting materials, doping materials, hole injecting materials and electron injecting materials can be used in the light emitting layer. The organic EL element has a multi-layer structure,
It is possible to prevent a decrease in brightness and life due to quenching. If necessary, a light emitting material, another doping material, a hole injecting material, and an electron injecting material can be used in combination. Further, by using other doping materials, it is possible to improve the light emission brightness and the light emission efficiency, and obtain red or white light emission. Further, by using it in combination with another doping material that contributes to phosphorescence, it is possible to improve the conventional emission brightness and emission efficiency. Further, the hole injection layer, the light emitting layer, and the electron injection layer may each be formed of a layer structure of two or more layers. In that case, in the case of a hole injection layer, a layer that injects holes from the electrode is called a hole injection layer, and a layer that receives holes from the hole injection layer and transports the holes to the light emitting layer is called a hole transport layer. . Similarly, in the case of an electron injection layer, a layer that injects electrons from an electrode is called an electron injection layer, and a layer that receives electrons from the electron injection layer and transports electrons to the light emitting layer is called an electron transport layer. Each of these layers is selected and used according to factors such as the energy level of the material, heat resistance, and adhesion to the organic compound layer or the metal electrode. Further, the organic compound layer preferably contains 1 to 70% by weight of the aromatic compound represented by the general formula (1). If the content is less than 1% by weight, the effect of the present invention cannot be obtained, and if it exceeds 70% by weight, durability and luminous efficiency tend to be lowered.

As the light emitting material or host material which can be used in the organic compound layer together with the compound of the general formula (1) of the present invention, anthracene, naphthalene, phenanthrene, pyrene, tetracene, coronene, chrysene, fluorescein, perylene, phthaloperylene, naphthaloperylene, Perinone, phthaloperinone, naphthaloperinone, diphenylbutadiene, tetraphenylbutadiene, coumarin,
Oxadiazole, aldazine, bisbenzoxazoline, bisstyryl, pyrazine, cyclopentadiene, quinoline metal complex, aminoquinoline metal complex, benzoquinoline metal complex, imine, diphenylethylene, vinylanthracene, diaminocarbazole, pyran, thiopyran, polymethine, merocyanine , Imidazole chelated oxinoid compounds, quinacridone, rubrene, stilbene derivatives, fluorescent dyes, and the like, but are not limited thereto.

The hole-injecting material has the ability to transport holes, has the effect of injecting holes from the anode, and has an excellent effect of injecting holes into the light-emitting layer or the light-emitting material. A compound that prevents excitons from moving to the electron injection layer or the electron injection material and has an excellent thin film forming ability is preferable. Specifically, phthalocyanine derivative, naphthalocyanine derivative, porphyrin derivative, oxazole, oxadiazole, triazole, imidazole, imidazolone, imidazolethione, pyrazoline, pyrazolone, tetrahydroimidazole, oxazole, oxadiazole,
Hydrazone, acylhydrazone, polyarylalkane, stilbene, butadiene, benzidine-type triphenylamine, styrylamine-type triphenylamine, diamine-type triphenylamine, etc., and their derivatives and polyvinylcarbazole, polysilane, conductive polymers, etc. Examples include, but are not limited to, molecular materials.

Among these hole injecting materials, a more effective hole injecting material is an aromatic tertiary amine derivative or a phthalocyanine derivative. Specific examples of the aromatic tertiary amine derivative include triphenylamine, tritolylamine, tolyldiphenylamine, N, N′-diphenyl-N, N ′-(3-methylphenyl) -1,1′-biphenyl-4, 4'-diamine, N, N, N ', N'-
(4-methylphenyl) -1,1′-phenyl-4,
4'-diamine, N, N, N ', N'-(4-methylphenyl) -1,1'-biphenyl-4,4'-diamine, N, N'-diphenyl-N, N'-dinaphthyl-
1,1'-biphenyl-4,4'-diamine, N, N '
-(Methylphenyl) -N, N '-(4-n-butylphenyl) -phenanthrene-9,10-diamine, N,
N-bis (4-di-4-tolylaminophenyl) -4-
Phenyl-cyclohexane and the like, or oligomers or polymers having an aromatic tertiary amine skeleton thereof, but are not limited thereto. Specific examples of the phthalocyanine (Pc) derivative include H ₂ Pc and Cu.
Pc, CoPc, NiPc, ZnPc, PdPc, Fe
Pc, MnPc, ClAlPc, ClGaPc, CLI
nPc, ClSnPc, Cl ₂ SiPc, (HO) Al
Pc, (HO) GaPc, VOPc, TiOPc, Mo
It is a phthalocyanine derivative such as OPc, GaPc-O-GaPc and a naphthalocyanine derivative, but is not limited thereto.

The electron injecting material has an ability to transport electrons, has an electron injecting effect from the cathode, and an excellent electron injecting effect to the light emitting layer or the light emitting material, and excites excitons generated in the light emitting layer. A compound that prevents migration to the hole injection layer and has an excellent thin film forming ability is preferable. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, quinoxaline, fluorenylidene methane, anthraquinodimethane, anthrone and the like. However, the present invention is not limited to these. Further, the charge injection property can be improved by adding an electron accepting substance to the hole injecting material and an electron donating substance to the electron injecting material.

Among these electron injecting materials, a more effective electron injecting material is a metal complex compound or a nitrogen-containing five-membered ring derivative. Specific examples of the metal complex compound include
8-hydroxyquinolinato lithium, bis (8-hydroxyquinolinato) zinc, bis (8-hydroxyquinolinato) copper, bis (8-hydroxyquinolinato) manganese, tris (8-hydroxyquinolinato) aluminum , Tris (2-methyl-8-hydroxyquinolinato) aluminum, tris (8-hydroxyquinolinato) gallium, bis (10-hydroxybenzo [h]
Quinolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc, bis (2-methyl-8)
-Quinolinato) chlorogallium, bis (2-methyl-)
8-quinolinato) (o-cresolato) gallium, bis (2-methyl-8-quinolinato) (1-naphtholato) aluminum, bis (2-methyl-8-quinolinato) (2-naphtholato) gallium and the like,
It is not limited to these.

The nitrogen-containing five-membered derivative is preferably an oxazole, thiazole, oxadiazole, thiadiazole or triazole derivative. In particular,
2,5-bis (1-phenyl) -1,3,4-oxazole, dimethyl POPOP, 2,5-bis (1-phenyl) -1,3,4-thiazole, 2,5-bis (1-phenyl) ) -1,3,4-Oxadiazole, 2- (4 '
-Tert-butylphenyl) -5- (4 "-biphenyl) 1,3,4-oxadiazole, 2,5-bis (1
-Naphthyl) -1,3,4-oxadiazole, 1,4
-Bis [2- (5-phenyloxadiazolyl)] benzene, 1,4-bis [2- (5-phenyloxadiazolyl) -4-tert-butylbenzene], 2- (4 '
-Tert-butylphenyl) -5- (4 "-biphenyl) -1,3,4-thiadiazole, 2,5-bis (1
-Naphthyl) -1,3,4-thiadiazole, 1,4-
Bis [2- (5-phenylthiadiazolyl)] benzene, 2- (4'-tert-butylphenyl) -5- (
4 "-biphenyl) -1,3,4-triazole, 2,
5-bis (1-naphthyl) -1,3,4-triazole, 1,4-bis [2- (5-phenyltriazolyl)
Examples thereof include, but are not limited to, benzene and the like.

The organic EL device of the present invention comprises an organic compound layer and
An inorganic compound layer may be provided between the electrodes. Mineralization
Preferred inorganic compounds used in the compound layer include alkanes.
Potassium metal oxide, alkaline earth oxide, rare earth oxide,
Alkali metal halide, alkaline earth halogenation
Compounds, rare earth halides, SiO_X, AlO_X, SiN
_X, SiON, AlON, GeO_X, LiO_X, LiO
N, TiO_X, TiON, TaO_X, TaON, TaN
_X, C, various oxides, nitrides, oxynitrides, etc.
It In particular, as a component of the layer in contact with the anode, SiO_X, A
10_X, SiN_X, SiON, AlON, GeO_X, C
Is preferable because it forms a stable injection interface layer. Also especially yin
The components of the layer in contact with the electrodes include LiF and MgF₂, Ca
F₂, MgF₂, NaF are preferred.

In the organic EL device of the present invention, the organic compound layer contains, in addition to the compound of the general formula, at least one of a light emitting material, a doping material, a hole injection material and an electron injection material in the same layer. May be. In order to improve the stability of the organic EL device obtained by the present invention against temperature, humidity, atmosphere, etc., a protective layer may be provided on the surface of the device or the entire device may be protected with silicone oil, resin, etc. Is also possible. As the conductive material used for the anode of the organic EL element, one having a work function larger than 4 eV is suitable, and carbon, aluminum, vanadium,
Iron, cobalt, nickel, tungsten, silver, gold, platinum, palladium and their alloys, ITO substrates, NE
Metal oxides such as tin oxide and indium oxide used for the SA substrate, and organic conductive resins such as polythiophene and polypyrrole are used. As the conductive material used for the cathode, one having a work function smaller than 4 eV is suitable, and magnesium, calcium, tin, lead, titanium, yttrium, lithium, ruthenium, manganese, aluminum and the like and alloys thereof are used. However,
It is not limited to these. Alloys include magnesium / silver, magnesium / indium, lithium /
Typical examples are aluminum and the like, but the invention is not limited thereto. The alloy ratio is controlled by the temperature of the vapor deposition source, the atmosphere, the degree of vacuum, etc., and is selected as an appropriate ratio. The anode and the cathode may be formed in a layered structure of two or more layers if necessary.

In the organic EL device of the present invention, it is desirable that at least one surface is sufficiently transparent in the emission wavelength region of the device in order to emit light efficiently. It is also desirable that the substrate is transparent. The transparent electrode is made of the above-mentioned conductive material and is set by a method such as vapor deposition or sputtering so as to ensure a predetermined translucency. The electrode on the light emitting surface preferably has a light transmittance of 10% or more. The substrate is not limited as long as it has mechanical and thermal strength and is transparent, and examples thereof include a glass substrate and a transparent resin film. As the transparent resin film, polyethylene, ethylene-vinyl acetate copolymer, ethylene-vinyl alcohol copolymer, polypropylene,
Polystyrene, polymethylmethacrylate, polyvinyl chloride, polyvinyl alcohol, polyvinyl butyral, nylon, polyether ether ketone, polysulfone, polyether sulfone, tetrafluoroethylene-perfluoroalkyl vinyl ether copolymer, polyvinylfluoride, tetrafluoroethylene -Ethylene copolymer, tetrafluoroethylene-hexafluoropropylene copolymer, polychlorotrifluoroethylene, polyvinylidene fluoride, polyester, polycarbonate, polyurethane, polyimide, polyetherimide, polyimide, polypropylene and the like.

Each layer of the organic EL device of the present invention may be formed by any one of dry film forming methods such as vacuum deposition, sputtering, plasma and ion plating, and wet film forming methods such as spin coating, dipping and flow coating. Can be applied. The film thickness is not particularly limited, but it needs to be set to an appropriate film thickness. If the film thickness is too thick, a large applied voltage is required to obtain a constant light output, resulting in poor efficiency. If the film thickness is too thin, pinholes and the like will occur, and even if an electric field is applied, sufficient emission brightness cannot be obtained. The normal film thickness is preferably in the range of 5 nm to 10 μm, more preferably in the range of 10 nm to 0.2 μm.

In the case of the wet film forming method, the materials forming each layer are ethanol, chloroform, tetrahydrofuran,
The thin film is formed by dissolving or dispersing in a suitable solvent such as dioxane, and any solvent may be used. Also,
Appropriate resins and additives may be used in any of the organic thin film layers in order to improve film-forming properties and prevent pinholes in the film. Examples of usable resins include insulating resins such as polystyrene, polycarbonate, polyarylate, polyester, polyamide, polyurethane, polysulfone, polymethylmethacrylate, polymethylacrylate and cellulose, and copolymers thereof, poly-N-vinyl. Examples thereof include photoconductive resins such as carbazole and polysilane, and conductive resins such as polythiophene and polypyrrole. Also,
Examples of the additives include antioxidants, ultraviolet absorbers, plasticizers and the like.

By using the compound of the present invention in the organic compound layer of the organic EL device, the color purity and the luminous efficiency are high,
It is possible to obtain an organic EL element which has a long life and emits reddish light. INDUSTRIAL APPLICABILITY The organic EL device of the present invention is useful for flat light emitters such as flat panel displays for wall-mounted televisions, light sources for copiers, printers, backlights of liquid crystal displays, instruments or the like, display plates, marker lights, accessories and the like.

[0040]

EXAMPLES Next, the present invention will be described in more detail with reference to examples. Production Example 1 (Synthesis of Compound (A)) The chemical reaction formula in the synthetic process of Compound (A) is shown below.

[Chemical 7]

In a 100 ml three neck flask,
2.0 g of 5,11-dibromo-naphthacene (5.18 m
mol), N, N-diphenyl-N'-p-tolylamine 3.99 g (11.4 mmol), tris (dibenzylideneacetone) dipalladium (0) 124 mg.
(0.136 mmol), (S)-(-)-BINAP
(2,2'-bis- (diphenylphosphino) -1,
170 mg (0.272 mmo) of 1'-binaphthyl)
1), 1.19 g (12.4 g) of sodium t-butoxide.
(80 mmol) and substituted with argon, 80 ml of dehydrated xylene was added, the temperature was raised to 125 ° C. with stirring, and the mixture was further stirred for 7 hours. After completion of the reaction, the mixture was cooled to room temperature, 100 ml of dichloromethane was added, and the mixture was stirred at room temperature for a while and then filtered. The filtrate was concentrated, and the target product was separated by silica gel column chromatography using hexane and toluene as solvents. The solvent was removed, the obtained residue was further recrystallized with a mixed solvent of toluene and ethanol, and the precipitated crystal was separated by filtration and dried, and 3.28 g (3.
55 mmol) of compound (A) was obtained (yield 69%).
Next, the obtained compound (A) was treated at 350 ° C. and 3.6 × 10 ^−6.
Purification by degassing with Torr gave a purple powder. The results of field diffusion (FD) mass analysis, HPLC purity and UVAbs of the obtained compound (A) are shown below. FD mass analysis: 924 (M ⁺ , bp), 462 (M ²⁺ ) HPLC purity: 95% UVAbs: 558 nm (toluene)

Production Example 2 (Synthesis of Compounds (B) and (B ′)) The chemical reaction formulas in the synthetic process of the compounds (B) and (B ′) are shown below.

[Chemical 8]

In a 100 ml three neck flask,
2.0 g (5.59 m) of 3,8-dibromo-naphthacene and 3,9-dibromo-naphthacene mixture (mixing ratio 7: 3)
mol), N- (4-dimethylaminophenyl) -p-
2.71 g (12.0 mmol) of toluidine, tris (dibenzylideneacetone) dipalladium (0) 77 m
g (0.084 mmol), (S)-(-)-BINA
P (2,2'-bis- (diphenylphosphino) -1,
1'-binaphthyl) 104 mg (0.168 mmo)
l), 1.3 g of sodium t-butoxide (13.5 m
(mol) and replaced with argon, and then dehydrated toluene 7
0 ml was added, the temperature was raised to 115 ° C. with stirring, and the mixture was further stirred for 7 hours. After completion of the reaction, the mixture was cooled to room temperature, 100 ml of dichloromethane was added, and the mixture was stirred at room temperature for a while and then filtered. The filtrate was concentrated, and the target product was separated by silica gel column chromatography using dichloromethane as a solvent. The solvent was removed, the obtained residue was further recrystallized with a mixed solvent of toluene and ethanol, and the precipitated crystal was separated by filtration and dried to give 3.11 g (4.7 g).
8 mmol) of compounds (B) and (B ′) were obtained (yield 86%). Next, the obtained compounds (B) and (B ′) 2.
5 g was sublimated and purified at 400 ° C. and 5.0 × 10 ⁻⁶ Torr to obtain 2.0 g of red powder. Obtained compound (B)
And (B ') FD mass analysis, HPLC purity and UVA
The measurement results of bs are shown below. FD mass analysis: 650 (M ⁺ , bp) HPLC purity: 96% UVAbs: 521 nm (toluene)

Production Example 3 (Synthesis of Compounds (C) and (C ')) The chemical reaction formulas in the synthetic process of the compounds (C) and (C') are shown below.

[Chemical 9]

In a 100 ml three-necked flask, 3,10-dibromo-7,14-diphenylacenaphtho [1,2-k] fluoranthene, 3,11-dibromo-
2.0 g (3.15 m) of 7,14-diphenylacenaphtho [1,2-k] fluoranthene mixture (mixing ratio 7: 3)
mol), N- (4-dimethylaminophenyl) -p-
Toluidine 1.57 g (6.93 mmol), tris (dibenzylideneacetone) dipalladium (0) 44 m
g (0.047 mmol), (S)-(-)-BINA
P (2,2'-bis- (diphenylphosphino) -1,
1'-binaphthyl) 59 mg (0.095 mmol),
Sodium t-butoxide 727 mg (7.56 mmo)
After l) was charged and the atmosphere was replaced with argon, 40 ml of dehydrated toluene was added, the temperature was raised to 115 ° C with stirring, and the mixture was further stirred for 7 hours. After the reaction is completed, cool to room temperature, and
0 ml of dichloromethane was added, and the mixture was stirred at room temperature for a while and then filtered. The filtrate was concentrated, and the target product was separated by silica gel column chromatography using dichloromethane as a solvent. The solvent was removed, the obtained residue was further recrystallized with a mixed solvent of toluene and ethanol, and the precipitated crystal was separated by filtration and dried, and 2.65 g (2.86 mmo)
l) Compounds (C) and (C ′) were obtained (yield 91
%). Next, 1.2 g of the obtained compounds (C) and (C ′)
Was purified by degassing at 350 ° C. and 5.0 × 10 ⁻⁶ Torr to obtain a purple powder. F of the obtained compounds (C) and (C ′)
The results of D-mass analysis, HPLC purity and UVAbs are shown below. FD mass analysis: 926 (M ⁺ , bp), 463 (M ²⁺ ) HPLC purity: 95% UVAbs: 546 nm (toluene)

Production Example 4 (Synthesis of Compounds (D) and (D ')) The chemical reaction formulas in the synthetic process of the compounds (D) and (D') are shown below.

[Chemical 10]

In a 100 ml three-necked flask,
3,10-Dibromo-7,14-diphenylacenaphtho [1,2-k] fluoranthene, 3,11-dibromo-
3.0 g (4.72 m) of 7,14-diphenylacenaphtho [1,2-k] fluoranthene mixture (mixing ratio 9: 1)
mol), N, N-ditolylamine 1.0 g (5.1
0 mmol), N- (4-dimethylaminophenyl)-
1.15 g (5.10 mmol) of p-toluidine, tris (dibenzylideneacetone) dipalladium (0) 64
mg (0.07 mmol), (S)-(-)-BINA
P (2,2'-bis- (diphenylphosphino) -1,
1'-binaphthyl) 88 mg (0.14 mmol), sodium t-butoxide 1.1 g (11.4 mmol)
Was charged and the atmosphere was replaced with argon. Then, 60 ml of dehydrated toluene was added, the temperature was raised to 110 ° C. with stirring, and the mixture was further stirred for 6 hours. After completion of the reaction, the mixture was cooled to room temperature, 60 ml of toluene was added, stirred at room temperature for a while, and then filtered. The organic layer was dried by adding magnesium sulfate, filtered and concentrated, and the residue obtained was separated and purified by column chromatography using hexane and toluene. The obtained solid was recrystallized with toluene and acetonitrile to obtain 1.57 g (1.72 mmol) of compounds (D) and (D ′) (yield 37%). Next, the obtained compounds (D) and (D ′) were treated at 350 ° C. and 4.8 × 10 ⁻⁶ Tor.
It was deaerated and purified by r to obtain a purple powder. The results of FD mass analysis, HPLC purity and UVAbs of the obtained compounds (D) and (D ′) are shown below. FD mass analysis: 914 (M ⁺ , bp), 457 (M ²⁺ ) HPLC purity: 98% UVAbs: 534 nm (toluene)

Production Example 5 (Synthesis of Compounds (E) and (E ')) The chemical reaction formulas in the synthetic process of the compounds (E) and (E') are shown below.

[Chemical 11]

In a 100 ml three neck flask,
3,10-Dibromo-7,14-diphenylacenaphtho [1,2-k] fluoranthene, 3,11-dibromo-
2.0 g (3.15 m) of 7,14-diphenylacenaphtho [1,2-k] fluoranthene mixture (mixing ratio 8: 2)
mol), 3,3′-bis (dimethylaminophenyl)
1.77 g (6.93 mmol) of amine, 44 mg of tris (dibenzylideneacetone) dipalladium (0)
(0.047 mmol), (S)-(-)-BINAP
(2,2'-bis- (diphenylphosphino) -1,
1'-binaphthyl) 59 mg (0.095 mmol),
Sodium t-butoxide 696 mg (7.24 mmo
After l) was added and the atmosphere was replaced with argon, 50 ml of dehydrated toluene was added, the temperature was raised to 115 ° C with stirring, and the mixture was further stirred for 7 hours and a half. After completion of the reaction, the mixture was cooled to room temperature and filtered. The filtrate was concentrated, and the obtained residue was separated and purified by chromatography using 50 g of silica gel, developed with a mixed solvent of hexane and toluene. After concentrating the fraction of the target substance, recrystallizing it with a mixed solvent of toluene and ethanol, the precipitated crystals were separated by filtration and dried to give 2.63 g.
(2.64 mmol) of compounds (E) and (E ′) were obtained (yield 84%). Next, 1.0 g of the obtained compounds (E) and (E ′) was heated at 350 ° C. and 4.8 × 10 ⁻⁶ Torr.
It was deaerated and purified by to obtain a dark red solid. The results of FD mass analysis, HPLC purity and UVAbs of the obtained compounds (E) and (E ′) are shown below. FD mass analysis: 984 (M ⁺ , bp) HPLC purity: 98% UVAbs: 515 nm (toluene)

Example 1 (Production of Organic EL Element) A transparent electrode made of indium tin oxide having a film thickness of 120 nm was provided on a glass substrate having a size of 25 × 75 × 1.1 mm. The glass substrate was irradiated with ultraviolet rays and ozone to be washed, and then the glass substrate was placed in a vacuum vapor deposition apparatus. First, the following TPD74 was deposited to a thickness of 60 nm, and then the following NPD was deposited to a thickness of 20 nm thereon. Then, the compounds (C) and (C ′) as light emitting materials
And the following DPVDPAN

[Chemical 12] Was co-evaporated at a weight ratio of 2:40 (the weight of the compounds (C) and (C ′) was 3.7% by weight) to form a luminescence medium layer having a thickness of 50 nm. Next, Alq (aluminum complex of 8-hydroxyquinoline) was vapor-deposited to a thickness of 10 nm. T
PD74, NPD, compounds (C) and (C ') and the following D
PVDPAN and Alq are a hole injection layer, a hole transport layer, a light emitting medium layer and an electron injection layer, respectively. Next, an alkali metal halide, LiF, was evaporated to a thickness of 0.2 nm, and then aluminum was evaporated to a thickness of 150 nm. This Al / LiF functions as a cathode, and thus an organic EL element was produced. When an energization test was conducted on the obtained device, the voltage was 8.5 V and the current density was 1
Luminance of 97.9 cd / m at 3.35 mA / cm ² .
A red emission of ² is obtained, and chromaticity coordinates (0.67, 0.3
3), and the luminous efficiency was 0.73 cd / A.

Example 2 (Production of Organic EL Element) In Example 1, the compounds (C) and (C ′) as the light emitting material and the following DPVTP were used.

[Chemical 13] Was similarly co-deposited at a weight ratio of 2:40 (the weight of the compounds (C) and (C ′) was 3.6% by weight) to produce an organic EL device in the same manner. When an energization test was conducted on the obtained device, the voltage was 8.0 V and the current density was 14.2.
At ² mA / cm ² , red light emission with an emission luminance of 119 cd / m ² was obtained, the chromaticity coordinate (0.67, 0.33) and the light emission efficiency were 0.84 cd / A.

Example 3 (Production of Organic EL Element) In Example 1, the compounds (D) and (D ′) and DPVDPAN were used as the light emitting materials in a weight ratio of 2:40 (compounds (D) and (D ′)). An organic EL device was produced in the same manner except that the vapor deposition was carried out at a weight of 3.7% by weight. When an energization test was conducted on the obtained device, red light emission with a light emission luminance of 98.0 cd / m ² was obtained at a voltage of 9.0 V and a current density of 9.80 mA / cm ² , and the chromaticity coordinate (0.66 , 0.34), and the luminous efficiency is 1.00 cd / A.
Met.

Example 4 (Production of Organic EL Element) In Example 1, the compounds (D) and (D ′) and DPVTP were used as the light emitting materials in a weight ratio of 2:40 (compounds (D) and (D ′)). An organic EL device was produced in the same manner except that the vapor deposition was performed at a weight of 3.5% by weight). When an energization test was conducted on the obtained device, red light emission with a light emission luminance of 94.9 cd / m ² was obtained at a voltage of 8.0 V and a current density of 8.27 mA / cm ² , and the chromaticity coordinate (0. 66, 0.34), and the luminous efficiency is 1.15 cd / A.
Met.

Comparative Example 1 In Example 1, the following Ru2 was used as the light emitting material.

[Chemical 14] And Alq were co-deposited at a weight ratio of 1:40 (Ru2 weight 2.0% by weight) to prepare an organic EL device in the same manner. When an energization test was conducted on the obtained device, a current of 28.0 mA / cm ² was flowing at a voltage of 10 V, and the applied voltage was higher than those of the devices of Examples 1 to 4.
Further, the emission luminance is 116 cd / m ² , the emission efficiency is 0.41 cd / A, which is low, and the chromaticity coordinate is (0.
67, 0.32).

Comparative Example 2 In Example 1, as a light emitting material, International Publication No. WO0
The following structural formula (A-16) described in 1/23497

[Chemical 15] The weight ratio of the amine-based aromatic compound represented by
An organic EL device was produced in the same manner except that 10 ((A-16) weight 5.0% by weight) was co-evaporated. When an energization test was conducted on the obtained device, it was found that the emission luminance was 121 cd / m ² and the emission efficiency was 3.31 cd / A at a voltage of 7.5 V, a current density of 3.65 mA / cm ² , and When the degree coordinate was (0.63, 0.37), the color purity was poor and red-orange light was emitted.

Comparative Example 3 In Example 1, as a light emitting material, International Publication No. WO0
The weight ratio of the amine-based aromatic compound represented by the structural formula (A-16) described in 1/23497 and DPVDPAN is 2:
40 ((A-16) weight 4.0% by weight) was prepared in the same manner as above, except that the organic EL device was produced. When an energization test was conducted on the obtained device, the light emission luminance was 86.6 cd / m ² and the light emission efficiency was 11.21 cd / m ² at a voltage of 6.0 V and a current density of 0.77 mA / cm ² .
Although it was A, the chromaticity coordinate was (0.56, 0.43), the color purity was poor, and orange light was emitted.

[0057]

As described in detail above, the organic EL device of the present invention is a novel aromatic compound in which an electron donating substituent is further introduced onto an aromatic amino group bonded to a mother skeleton having a specific structure. By using the group compound, the color purity is high, the light emission luminance and the light emission efficiency are high when driven at a low voltage, and the red light is emitted.

   ─────────────────────────────────────────────────── ─── Continued front page    (72) Inventor Hosokawa Gideo             1280 Kamizumi, Sodegaura, Chiba Prefecture (72) Inventor Tadashi Kusumoto             1280 Kamizumi, Sodegaura, Chiba Prefecture F-term (reference) 3K007 AB02 AB03 AB04 AB06 EB00                 4H006 AA01 AB92

Claims (7)

[Claims] 1. A novel aromatic compound having an amino group represented by the following general formula (1). [Chemical 1] (In the general formula (1), X ₁ is a substituted or unsubstituted divalent condensed aromatic ring having 16 to 60 carbon atoms, Ar _{1 to} Ar.
₄ are each independently substituted or unsubstituted 6 carbon atoms
To 30 aromatic rings, and at least one of Ar _{1 to} Ar ₄ is an amino group represented by the following general formula (2). [Chemical 2] (In the general formula (2), X ₂ represents a substituted or unsubstituted divalent aromatic ring having 6 to 30 carbon atoms, R ₁ and R ₂ are each independently a substituted or unsubstituted straight chain, A branched or cyclic alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted aromatic ring having 6 to 30 carbon atoms, R ₁ and R ₂ may form a ring. 2. The novel aromatic compound according to claim 1, which is a luminescent compound. 3. An organic electroluminescence device having a light emitting layer or a plurality of organic compound layers including a light emitting layer between a pair of electrodes, wherein at least one of the organic compound layers is defined in claim 1 or 2. An organic electroluminescence device containing an aromatic compound represented by the general formula (1). 4. The organic electroluminescence device according to claim 3, wherein the organic compound layer is a hole transport layer and / or a light emitting layer. 5. The organic electroluminescence device according to claim 3, wherein the organic compound layer contains 1 to 70% by weight of the aromatic compound represented by the general formula (1). 6. The organic electroluminescence device according to claim 3, further comprising an inorganic compound layer between the organic compound layer and the electrode. 7. The light emission color is reddish light emission.
5. The organic electroluminescence device according to any one of 1.